# Electronic Supplementary Material (ESI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 2023

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_mo_lz_zjy_jy202_1_300k_0ma_a
_database_code_depnum_ccdc_archive 'CCDC 2235119'
loop_
_audit_author_name
_audit_author_address
alkynyl
;Sichuan university
China
;
_audit_update_record             
;
2023-01-09 deposited with the CCDC.	2023-06-01 downloaded from the CCDC.
;
_audit_creation_date             2022-10-18
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C18 H18 O2 S'
_chemical_formula_sum            'C18 H18 O2 S'
_chemical_formula_weight         298.38
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/n 1'
_space_group_name_Hall           '-P 2yn'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   11.7968(3)
_cell_length_b                   7.4154(2)
_cell_length_c                   18.6524(5)
_cell_angle_alpha                90
_cell_angle_beta                 104.9740(10)
_cell_angle_gamma                90
_cell_volume                     1576.27(7)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9894
_cell_measurement_temperature    290(2)
_cell_measurement_theta_max      27.311
_cell_measurement_theta_min      2.260
_shelx_estimated_absorpt_T_max   0.960
_shelx_estimated_absorpt_T_min   0.941
_exptl_absorpt_coefficient_mu    0.207
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6544
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1281 before and 0.0640 after correction.
The Ratio of minimum to maximum transmission is 0.8777.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.257
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             632
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.2
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0655
_diffrn_reflns_av_unetI/netI     0.0359
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            36614
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.535
_diffrn_reflns_theta_min         2.261
_diffrn_ambient_temperature      290.0
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_source_current           1.4
_diffrn_source_power             0.07
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2820
_reflns_number_total             3618
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT V8.40B (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.40B (?, 2016)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2014/7 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.182
_refine_diff_density_min         -0.338
_refine_diff_density_rms         0.040
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.029
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     193
_refine_ls_number_reflns         3618
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0549
_refine_ls_R_factor_gt           0.0395
_refine_ls_restrained_S_all      1.029
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0480P)²+0.3618P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0996
_refine_ls_wR_factor_ref         0.1095
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C009(H009), C00B(H00B), C00C(H00C), C00D(H00D), C00E(H00E), C00F(H00F),
 C00I(H00L), C00J(H00M), C00K(H00N)
2.b Idealised Me refined as rotating group:
 C00G(H00A,H00G,H00H), C00H(H00I,H00J,H00K), C00L(H00O,H00P,H00Q)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
S01 S 0.31350(3) 0.38127(6) 0.59001(2) 0.04905(14) Uani 1 1 d . . . . .
O002 O 0.35737(12) 0.55282(16) 0.57361(7) 0.0684(4) Uani 1 1 d . . . . .
O003 O 0.18988(10) 0.3474(2) 0.56482(7) 0.0706(4) Uani 1 1 d . . . . .
C004 C 0.35680(13) 0.3513(2) 0.68690(8) 0.0429(3) Uani 1 1 d . . . . .
C005 C 0.73582(13) 0.2914(2) 0.64530(9) 0.0466(4) Uani 1 1 d . . . . .
C006 C 0.61476(13) 0.2505(2) 0.61046(9) 0.0482(4) Uani 1 1 d . . . . .
C007 C 0.51358(13) 0.2260(2) 0.58284(8) 0.0463(3) Uani 1 1 d . . . . .
C008 C 0.38752(13) 0.2046(2) 0.54978(8) 0.0456(3) Uani 1 1 d . . . . .
C009 C 0.28353(13) 0.2639(2) 0.72303(9) 0.0483(4) Uani 1 1 d . . . . .
H009 H 0.2134 0.2131 0.6961 0.058 Uiso 1 1 calc R U . . .
C00A C 0.42076(15) 0.3247(2) 0.84067(9) 0.0526(4) Uani 1 1 d . . . . .
C00B C 0.46140(13) 0.4265(2) 0.72727(9) 0.0508(4) Uani 1 1 d . . . . .
H00B H 0.5101 0.4867 0.7032 0.061 Uiso 1 1 calc R U . . .
C00C C 0.31591(15) 0.2533(2) 0.79944(9) 0.0534(4) Uani 1 1 d . . . . .
H00C H 0.2661 0.1969 0.8238 0.064 Uiso 1 1 calc R U . . .
C00D C 0.49239(14) 0.4111(2) 0.80330(9) 0.0561(4) Uani 1 1 d . . . . .
H00D H 0.5632 0.4598 0.8303 0.067 Uiso 1 1 calc R U . . .
C00E C 0.77500(15) 0.3013(3) 0.72229(10) 0.0602(4) Uani 1 1 d . . . . .
H00E H 0.7243 0.2734 0.7515 0.072 Uiso 1 1 calc R U . . .
C00F C 0.81363(14) 0.3289(2) 0.60266(10) 0.0561(4) Uani 1 1 d . . . . .
H00F H 0.7889 0.3212 0.5512 0.067 Uiso 1 1 calc R U . . .
C00G C 0.34303(15) 0.0214(2) 0.56698(11) 0.0617(5) Uani 1 1 d . . . . .
H00A H 0.3594 0.0061 0.6198 0.093 Uiso 1 1 calc R U . . .
H00G H 0.3817 -0.0717 0.5464 0.093 Uiso 1 1 calc R U . . .
H00H H 0.2599 0.0142 0.5456 0.093 Uiso 1 1 calc R U . . .
C00H C 0.35603(16) 0.2430(3) 0.46604(9) 0.0646(5) Uani 1 1 d . . . . .
H00I H 0.2723 0.2440 0.4470 0.097 Uiso 1 1 calc R U . . .
H00J H 0.3889 0.1508 0.4414 0.097 Uiso 1 1 calc R U . . .
H00K H 0.3872 0.3582 0.4574 0.097 Uiso 1 1 calc R U . . .
C00I C 0.92791(16) 0.3778(3) 0.63688(12) 0.0680(5) Uani 1 1 d . . . . .
H00L H 0.9802 0.4017 0.6084 0.082 Uiso 1 1 calc R U . . .
C00J C 0.88878(16) 0.3522(3) 0.75519(11) 0.0690(5) Uani 1 1 d . . . . .
H00M H 0.9144 0.3602 0.8066 0.083 Uiso 1 1 calc R U . . .
C00K C 0.96437(16) 0.3911(3) 0.71267(13) 0.0701(5) Uani 1 1 d . . . . .
H00N H 1.0408 0.4267 0.7353 0.084 Uiso 1 1 calc R U . . .
C00L C 0.4551(2) 0.3109(3) 0.92392(10) 0.0809(6) Uani 1 1 d . . . . .
H00O H 0.4518 0.4282 0.9451 0.121 Uiso 1 1 calc R U . . .
H00P H 0.5335 0.2643 0.9403 0.121 Uiso 1 1 calc R U . . .
H00Q H 0.4019 0.2312 0.9396 0.121 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
S01 O002 1.4358(13) . ?
S01 O003 1.4340(12) . ?
S01 C004 1.7606(15) . ?
S01 C008 1.8386(15) . ?
C004 C009 1.386(2) . ?
C004 C00B 1.386(2) . ?
C005 C006 1.440(2) . ?
C005 C00E 1.392(2) . ?
C005 C00F 1.389(2) . ?
C006 C007 1.186(2) . ?
C007 C008 1.464(2) . ?
C008 C00G 1.520(2) . ?
C008 C00H 1.536(2) . ?
C009 H009 0.9300 . ?
C009 C00C 1.379(2) . ?
C00A C00C 1.382(2) . ?
C00A C00D 1.384(2) . ?
C00A C00L 1.504(2) . ?
C00B H00B 0.9300 . ?
C00B C00D 1.375(2) . ?
C00C H00C 0.9300 . ?
C00D H00D 0.9300 . ?
C00E H00E 0.9300 . ?
C00E C00J 1.377(2) . ?
C00F H00F 0.9300 . ?
C00F C00I 1.383(2) . ?
C00G H00A 0.9600 . ?
C00G H00G 0.9600 . ?
C00G H00H 0.9600 . ?
C00H H00I 0.9600 . ?
C00H H00J 0.9600 . ?
C00H H00K 0.9600 . ?
C00I H00L 0.9300 . ?
C00I C00K 1.371(3) . ?
C00J H00M 0.9300 . ?
C00J C00K 1.369(3) . ?
C00K H00N 0.9300 . ?
C00L H00O 0.9600 . ?
C00L H00P 0.9600 . ?
C00L H00Q 0.9600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O002 S01 C004 107.79(7) . . ?
O002 S01 C008 108.00(8) . . ?
O003 S01 O002 118.52(8) . . ?
O003 S01 C004 108.36(7) . . ?
O003 S01 C008 106.94(7) . . ?
C004 S01 C008 106.66(7) . . ?
C009 C004 S01 120.40(11) . . ?
C00B C004 S01 119.23(12) . . ?
C00B C004 C009 120.23(14) . . ?
C00E C005 C006 120.19(14) . . ?
C00F C005 C006 120.57(15) . . ?
C00F C005 C00E 119.19(15) . . ?
C007 C006 C005 176.40(17) . . ?
C006 C007 C008 177.25(17) . . ?
C007 C008 S01 106.77(10) . . ?
C007 C008 C00G 112.12(13) . . ?
C007 C008 C00H 111.15(13) . . ?
C00G C008 S01 108.92(11) . . ?
C00G C008 C00H 111.98(14) . . ?
C00H C008 S01 105.51(11) . . ?
C004 C009 H009 120.4 . . ?
C00C C009 C004 119.21(14) . . ?
C00C C009 H009 120.4 . . ?
C00C C00A C00D 118.17(15) . . ?
C00C C00A C00L 120.80(17) . . ?
C00D C00A C00L 121.03(17) . . ?
C004 C00B H00B 120.4 . . ?
C00D C00B C004 119.28(15) . . ?
C00D C00B H00B 120.4 . . ?
C009 C00C C00A 121.49(15) . . ?
C009 C00C H00C 119.3 . . ?
C00A C00C H00C 119.3 . . ?
C00A C00D H00D 119.2 . . ?
C00B C00D C00A 121.60(15) . . ?
C00B C00D H00D 119.2 . . ?
C005 C00E H00E 120.0 . . ?
C00J C00E C005 119.99(17) . . ?
C00J C00E H00E 120.0 . . ?
C005 C00F H00F 120.1 . . ?
C00I C00F C005 119.86(17) . . ?
C00I C00F H00F 120.1 . . ?
C008 C00G H00A 109.5 . . ?
C008 C00G H00G 109.5 . . ?
C008 C00G H00H 109.5 . . ?
H00A C00G H00G 109.5 . . ?
H00A C00G H00H 109.5 . . ?
H00G C00G H00H 109.5 . . ?
C008 C00H H00I 109.5 . . ?
C008 C00H H00J 109.5 . . ?
C008 C00H H00K 109.5 . . ?
H00I C00H H00J 109.5 . . ?
H00I C00H H00K 109.5 . . ?
H00J C00H H00K 109.5 . . ?
C00F C00I H00L 119.9 . . ?
C00K C00I C00F 120.24(17) . . ?
C00K C00I H00L 119.9 . . ?
C00E C00J H00M 119.8 . . ?
C00K C00J C00E 120.37(18) . . ?
C00K C00J H00M 119.8 . . ?
C00I C00K H00N 119.8 . . ?
C00J C00K C00I 120.31(17) . . ?
C00J C00K H00N 119.8 . . ?
C00A C00L H00O 109.5 . . ?
C00A C00L H00P 109.5 . . ?
C00A C00L H00Q 109.5 . . ?
H00O C00L H00P 109.5 . . ?
H00O C00L H00Q 109.5 . . ?
H00P C00L H00Q 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
S01 C004 C009 C00C -175.51(12) . . . . ?
S01 C004 C00B C00D 176.71(13) . . . . ?
O002 S01 C004 C009 144.35(13) . . . . ?
O002 S01 C004 C00B -31.38(14) . . . . ?
O002 S01 C008 C007 58.31(12) . . . . ?
O002 S01 C008 C00G 179.58(11) . . . . ?
O002 S01 C008 C00H -60.04(13) . . . . ?
O003 S01 C004 C009 14.94(15) . . . . ?
O003 S01 C004 C00B -160.79(13) . . . . ?
O003 S01 C008 C007 -173.10(11) . . . . ?
O003 S01 C008 C00G -51.82(13) . . . . ?
O003 S01 C008 C00H 68.56(13) . . . . ?
C004 S01 C008 C007 -57.32(12) . . . . ?
C004 S01 C008 C00G 63.95(12) . . . . ?
C004 S01 C008 C00H -175.67(11) . . . . ?
C004 C009 C00C C00A -1.3(2) . . . . ?
C004 C00B C00D C00A -1.1(3) . . . . ?
C005 C00E C00J C00K -0.9(3) . . . . ?
C005 C00F C00I C00K -0.6(3) . . . . ?
C006 C005 C00E C00J -175.66(17) . . . . ?
C006 C005 C00F C00I 176.40(16) . . . . ?
C008 S01 C004 C009 -99.88(13) . . . . ?
C008 S01 C004 C00B 84.39(14) . . . . ?
C009 C004 C00B C00D 1.0(2) . . . . ?
C00B C004 C009 C00C 0.2(2) . . . . ?
C00C C00A C00D C00B 0.0(3) . . . . ?
C00D C00A C00C C009 1.2(2) . . . . ?
C00E C005 C00F C00I -0.9(3) . . . . ?
C00E C00J C00K C00I -0.7(3) . . . . ?
C00F C005 C00E C00J 1.7(3) . . . . ?
C00F C00I C00K C00J 1.5(3) . . . . ?
C00L C00A C00C C009 -179.57(16) . . . . ?
C00L C00A C00D C00B -179.24(17) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
